DK0648735T3 - Preparation of intermediate for vitamin A acetate - Google Patents

Preparation of intermediate for vitamin A acetate

Info

Publication number
DK0648735T3
DK0648735T3 DK94115331T DK94115331T DK0648735T3 DK 0648735 T3 DK0648735 T3 DK 0648735T3 DK 94115331 T DK94115331 T DK 94115331T DK 94115331 T DK94115331 T DK 94115331T DK 0648735 T3 DK0648735 T3 DK 0648735T3
Authority
DK
Denmark
Prior art keywords
formula
cho
methyl
preparation
acetoxytiglinaldehyde
Prior art date
Application number
DK94115331T
Other languages
Danish (da)
Inventor
Ulrich Zutter
Original Assignee
Hoffmann La Roche
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche
Application granted granted Critical
Publication of DK0648735T3 publication Critical patent/DK0648735T3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/40—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with ozone; by ozonolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/007—Esters of unsaturated alcohols having the esterified hydroxy group bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

A novel process for the preparation of gamma -acetoxytiglinaldehyde, which is known as an important starting material for the preparation of vitamin A acetate from a ( beta -ionylideneethyl)triphenylphosphonium halide and this aldehyde, consists in subjecting a pentenyn-3-ol of the formula HC IDENTICAL C-C(CH3)(OH)-CH=C(R)2 (II) wherein both Rs are either hydrogen or methyl to a selective ozonolysis in a lower alkanol R<1>OH wherein R<1> is C1-4-alkyl, hydrogenating the 2-hydroxy-2-methyl-3-butynal thus obtained of the formula HC IDENTICAL C-C(CH3)(OH)-CHO (III) and 1-alkoxyalkyl hydroperoxide of the formula (HOO)(R<1>)CR<2> (IV) possibly obtained as a by-product to the known 2-hydroxy-2-methyl-3-butenal of the formula H2C=CH-C(CH3)(OH)-CHO (V) catalytically and (for III) selectively, and converting this in a manner known per se to the gamma -acetoxytiglinaldehyde of the formula CH3COO-CH2CH=C(CH3)-CHO (I). The conversion of the butenal V to the aldehyde I can expediently be carried out by the known process steps acetalisation, acetylation, catalysed rearrangement and acid-catalysed hydrolysis.
DK94115331T 1993-10-13 1994-09-29 Preparation of intermediate for vitamin A acetate DK0648735T3 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH307793 1993-10-13

Publications (1)

Publication Number Publication Date
DK0648735T3 true DK0648735T3 (en) 1998-09-23

Family

ID=4248122

Family Applications (1)

Application Number Title Priority Date Filing Date
DK94115331T DK0648735T3 (en) 1993-10-13 1994-09-29 Preparation of intermediate for vitamin A acetate

Country Status (7)

Country Link
US (1) US5453547A (en)
EP (1) EP0648735B1 (en)
JP (1) JPH07324056A (en)
AT (1) ATE162785T1 (en)
DE (1) DE59405165D1 (en)
DK (1) DK0648735T3 (en)
ES (1) ES2113022T3 (en)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1142194C (en) * 2000-01-25 2004-03-17 阿克佐诺贝尔股份有限公司 Process to make aminated polyolefins
CN101723827B (en) * 2009-12-15 2012-11-21 上虞新和成生物化工有限公司 Preparation method of 4-acetoxyl-2-methyl-2-butylenoic aldehyde
CN102924276B (en) * 2011-08-10 2014-12-17 浙江医药股份有限公司维生素厂 Preparation method and intermediate hemiacetal of 2-methyl-2-acetoxy-3-butenyl-1-aldehyde
CN108997117B (en) * 2018-07-09 2021-07-23 万华化学集团股份有限公司 Novel method for preparing 4-acetoxyl-2-methyl-2-butenal

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE564339A (en) * 1957-02-05 1900-01-01
US3639437A (en) * 1967-08-08 1972-02-01 Basf Ag Production of carboxylic esters of beth-formylcrotyl alcohol
CH495320A (en) * 1967-08-08 1970-08-31 Basf Ag Process for the preparation of carboxylic acid esters of B-formylcrotyl alcohol
GB1172969A (en) * 1968-08-02 1969-12-03 Nii Sint Spirtov I Orch Produk Process for Ozonizing Unsaturated Compounds
CH605592A5 (en) * 1974-04-03 1978-09-29 Hoffmann La Roche
DE2513999A1 (en) * 1975-03-29 1976-10-07 Basf Ag Methylbutene dial 1-acetals prepn. - from crotonaldehyde, acetals useful as inters for carotenoids
DE2711381A1 (en) * 1977-03-16 1978-09-21 Basf Ag PROCESS FOR THE MANUFACTURING OF VINYL LACTIC ACID AND ITS ESTERS
SU825492A1 (en) * 1979-01-08 1981-04-30 Nii Khim Pri Go G Univ Im N I Method of acetaldehyde production
FR2689346B1 (en) * 1992-03-31 1994-06-10 Matra Communication COMMUNICATION METHOD BY RADIO WITH TIME MULTIPLEXING.

Also Published As

Publication number Publication date
US5453547A (en) 1995-09-26
EP0648735A1 (en) 1995-04-19
DE59405165D1 (en) 1998-03-05
ES2113022T3 (en) 1998-04-16
ATE162785T1 (en) 1998-02-15
JPH07324056A (en) 1995-12-12
EP0648735B1 (en) 1998-01-28

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